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Volume 69 
Part 6 
Pages o936-o937  
June 2013  

Received 10 February 2013
Accepted 16 May 2013
Online 22 May 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.038
wR = 0.112
Data-to-parameter ratio = 15.7
Details
Open access

3-{[5-(4-Chlorophenyl)-3-methyl-1H-pyrazol-1-yl]methyl}-4-m-tolyl-1H-1,2,4-triazole-5(4H)-thione

aDepartment of Chemistry, Government College University, Lahore 54000, Pakistan,bChemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, England,cChemistry Department, Faculty of Science, Minia University, El-Minia, Egypt,dPharmaceutical Chemistry Department, Faculty of Pharmacy, Al Azhar University, Egypt, and eFaculty of Pharmacy, Pharmaceutical Chemistry Department, Cairo University, Cairo, Egypt
Correspondence e-mail: maqsood.ahmed@gcu.edu.pk

In the title compound, C20H18ClN5S, the toluene and triazole rings are oriented almost perpendicular to each other, making a dihedral angle of 89.97 (9)°, whereas the dihedral angle between cholorophenyl and pyrazole rings is 54.57 (11)°. In the crystal, pairs of N-H...N hydrogen bonds link the molecules into inversion dimers. Weaker C-H...S and C-H...Cl interactions are also present.

Related literature

For medicinal applications of 1, 2, 4-triazoles, see: Lipinski (1983[Lipinski, Ch. A. (1983). J. Med. Chem. 26, 1-6.]); Ram & Vlietinck (1988[Ram, V. J. & Vlietinck, A. J. (1988). J. Heterocycl. Chem. 25, 253-256.]); Akahoshi et al. (1998[Akahoshi, F., Takeda, S., Okada, T., Kajii, M., Nishimura, H., Sugiura, M., Inoue, Y., Fukaya, C., Naito, Y., Imagawa, T. & Nakamura, N. (1998). J. Med. Chem. 41, 2985-2993.]); Young et al. (2001[Young, C. K., Ho, K. S., Ghilsoo, N., Hong, S. J., Hoon, K. S., Il, Ch. K., Hyup, K. J. & Deok-Chan, H. (2001). J. Antibiot. 54, 460-462.]); Ouyang et al. (2005[Ouyang, X., et al. (2005). Bioorg. Med. Chem. Lett. 15, 5154-5159.]); Dolzhenko et al. (2007[Dolzhenko, A. V., Dolzhenko, A. V. & Chui, W.-K. (2007). Heterocycles, 71, 429-436.]). For general background to the coordination chemistry of triazoles, see: Mishra et al. (1989[Mishra, L., Ram, V. J. & Kushwaha, D. S. (1989). Transition Met. Chem. 14, 384-386.]); Klingele & Brooker (2003[Klingele, M. H. & Brooker, S. (2003). Coord. Chem. Rev. 241, 119-132.]); Beckmann & Brooker (2003[Beckmann, U. & Brooker, S. (2003). Coord. Chem. Rev. 245, 17-29.]); Ferrer et al. (2004[Ferrer, S., Ballesteros, R., Sambartolome, A., Gonzales, M., Alzuet, G., Borras, J. & Liu, M. (2004). J. Inorg. Biochem. 98, 1436-1446.]); Castineiras & Garcia-Santos (2008[Castineiras, A. & Garcia-Santos, I. (2008). Z. Anorg. Allg. Chem. 634, 2907-2916.]).

[Scheme 1]

Experimental

Crystal data
  • C20H18ClN5S

  • Mr = 395.90

  • Monoclinic, P 21 /n

  • a = 8.328 (5) Å

  • b = 16.407 (5) Å

  • c = 14.759 (5) Å

  • [beta] = 99.509 (5)°

  • V = 1988.9 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.31 mm-1

  • T = 296 K

  • 0.61 × 0.53 × 0.52 mm

Data collection
  • Bruker APEXII CCD detector diffractometer

  • Absorption correction: analytical {SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.833, Tmax = 0.855

  • 38237 measured reflections

  • 3914 independent reflections

  • 3207 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.112

  • S = 1.04

  • 3914 reflections

  • 250 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N4-HN4...N1i 0.88 (2) 2.02 (2) 2.888 (2) 166 (2)
C6-H6...S1ii 0.93 3.00 3.790 (3) 144
C20-H14...Cl1iii 0.93 2.98 3.537 (4) 120
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) -x+2, -y, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GW2132 ).


Acknowledgements

GC University Lahore is gratefully acknowledged for the X-ray diffraction measurements. The authors are thankful to Manchester Metropolitan University and Alazhar University for supporting this study.

References

Akahoshi, F., Takeda, S., Okada, T., Kajii, M., Nishimura, H., Sugiura, M., Inoue, Y., Fukaya, C., Naito, Y., Imagawa, T. & Nakamura, N. (1998). J. Med. Chem. 41, 2985-2993.  [ISI] [CrossRef] [ChemPort] [PubMed]
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [ISI] [details]
Beckmann, U. & Brooker, S. (2003). Coord. Chem. Rev. 245, 17-29.  [ISI] [CrossRef] [ChemPort]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Castineiras, A. & Garcia-Santos, I. (2008). Z. Anorg. Allg. Chem. 634, 2907-2916.  [ChemPort]
Dolzhenko, A. V., Dolzhenko, A. V. & Chui, W.-K. (2007). Heterocycles, 71, 429-436.  [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Ferrer, S., Ballesteros, R., Sambartolome, A., Gonzales, M., Alzuet, G., Borras, J. & Liu, M. (2004). J. Inorg. Biochem. 98, 1436-1446.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Klingele, M. H. & Brooker, S. (2003). Coord. Chem. Rev. 241, 119-132.  [ISI] [CrossRef] [ChemPort]
Lipinski, Ch. A. (1983). J. Med. Chem. 26, 1-6.  [CrossRef] [ChemPort] [PubMed] [ISI]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Mishra, L., Ram, V. J. & Kushwaha, D. S. (1989). Transition Met. Chem. 14, 384-386.  [CrossRef] [ChemPort] [ISI]
Ouyang, X., et al. (2005). Bioorg. Med. Chem. Lett. 15, 5154-5159.  [CrossRef] [PubMed] [ChemPort]
Ram, V. J. & Vlietinck, A. J. (1988). J. Heterocycl. Chem. 25, 253-256.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Young, C. K., Ho, K. S., Ghilsoo, N., Hong, S. J., Hoon, K. S., Il, Ch. K., Hyup, K. J. & Deok-Chan, H. (2001). J. Antibiot. 54, 460-462.  [PubMed]


Acta Cryst (2013). E69, o936-o937   [ doi:10.1107/S1600536813013494 ]

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